


Honesty Is Always The Best Policy

by casgirlsam



Category: Supernatural
Genre: Confusing family dynamics, F/F, F/M, Fluff and Crack, M/M, Multi, Team Free Dads, The Author Regrets Nothing, cas and sam try to be the responsible parents, eileen and rowena flirt, everyone say a prayer for shelly, jack is too honest for the adults, mention of m/f/f threesome, she doesn't get paid nearly enough for this
Language: English
Status: Completed
Published: 2019-08-25
Updated: 2019-08-25
Packaged: 2020-09-26 08:35:43
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,259
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20386807
Author URL: https://archiveofourown.org/users/casgirlsam/pseuds/casgirlsam
Summary: This is the story of how Jack is no longer allowed to talk to strangers.---In which Jack ends up embarrassing his poor Dad Sam, but it works out for the best.





	Honesty Is Always The Best Policy

**Author's Note:**

> hello! i'm back over a year later with another sam fic because shut up he needs love
> 
> anyway this came to be because i was biking home from work and i was thinking about jack and his adorable lack of being able to lie about personal stuff. we started talking about it in the spn:trsf discord server
> 
> waitress: ok so if that’s your auntie eileen... where does your auntie rowena fit in?  
jack: hmm i’m not sure. sam are you also married to auntie rowena?  
sam: *chokes on his coffee*  
rowena and eileen: *exchange mischievous grins*
> 
> “I have three fathers and two of them are relatives. The other two are dating. And NOT related. Their mom is sort of my mom too, I think?“  
“Dont worry, she's younger than them.“  
“My grandfather is God“  
Ramdo waitress: OHkay then
> 
> “my one dad is also my uncle”  
“I also have two other dads,but I dont like them much. Well, technically it was only Lucifer possessing the president, I'm not entirely sure what the protocol is for that“  
Dean: JUST IGNORE HIM HE'S ON SOME HEAVY CRAP. Poor kid just got his wisdom dooth pulled
> 
> ANYWAY ENJOY

This is the story of how Jack is no longer allowed to talk to strangers.

Especially when strangers ask about his family.

* * *

It had been a normal after-case diner run. Sam had just wanted to go home, get some quality alone time with Eileen, but Jack had seen the tacky-looking diner that was all chrome on the outside with promises of 50’s rock n roll music and sticky vinyl booths and pulled the puppy dog face on all the adults in the car and that was that.

Sam really regretted teaching him that move.

Jack sat between Dean and Cas, grinning like the toddler that had gotten the toy he had asked nicely for. “Isn’t this nice? A family dinner!”

Sam’s earlier annoyance melted away at the sight of their son being excited about something as simple as a family dinner out. He smiled. “Yeah, Jack. It is.” He looked around at the others, their faces wearing matching guilty faces for being annoyed at Jack’s insistent detour. “Right, guys?”

They all murmured a variation of “Yes, of course!”

“Great idea, kid.” Dean reached out to muss up Jack’s hair. Jack giggled and shoved Dean’s hand away and fixed his hair.

And just like that, the tension the adults felt slipped away. Even Rowena was smiling fondly at the Winchester antics, Sam noted. Though she tried to hide it by looking at the menu like nothing happened.

Shortly after, a bubbly brunette with a smile that said “I genuinely try” but eyes that yelled “But I’ve been here since open because my coworkers don’t” came up to take their drink orders. Jack looked so disappointed when Sam vetoed lemonade and sweet tea, Sam found himself compromising again for the second time that day. “Ok fine you can have chocolate milk at least.”

When the waitress came back with everyone’s drinks and took their orders, Jack once again was met with resistance from one of his dads regarding sweet treats. Cas for once was at least trying to talk Jack out of an overly sweet meal, but Dean of course had to step in. “The kid’ll have the strawberry stack, please.” he said, smirking and handing the waitress the stack of menus.

The waitress giggled. “Y’all are such a cute family.” She walked off to put in their orders while Sam and Cas glared at Dean, conveying the message _ We’re not going to discuss this in front of Jack. _ And _ You’re in for it when we get home, Mr. Brat. _

Okay, that last part came from Cas but still.

Not soon enough for Sam, the food came out and once everyone was situated with their food, the waitress -- Shelly, her nametag said -- looked like she was bursting to ask them a question. “So what’s the story here? Who has the privilege of being this cutie’s parents?”

Sam watched as Dean tried to open his mouth, no doubt trying to find an explanation that wouldn’t scar the poor under-paid girl, but Jack beat him to it.

“That’s my dad Dean, his brother and my dad Sam, and my dad Cas.” He said, beaming proudly. He pointed to the two women on either side of Sam. “And that’s my auntie Eileen and my Auntie Rowena.”

Shelly, bless her, looked monetarily taken aback, but she grinned “O-oh that’s…. Quite the family.” She said, tone clearly trying to be encouraging but also understandably very confused.

Jack nodded. “Cas and Dean are married and Sam and Eileen are dating.”

Shelly tilted her head. “What about your Auntie Rowena? Is she someone’s…” Sam looked over to his left at Rowena and confirmed -- yep -- she was glaring at the poor girl. “... sister?” Shelly finished with visible gulp.

“Oh no,” replied Jack. “She’s not anyone’s sister.”

Sam opened his mouth to save the situation and poor poor sweet Shelly that didn’t deserve a confusing family tree dumped on her, but Jack once again was too fast. Sam sighed and resigned himself to watching Shelly’s brain implode.

“Actually, now that I think about it…” He turned to Sam. “Sam, are you dating Rowena too?”

Sam choked on his coffee while Eileen, who had been silently enjoying the whole exchange, giggled and exchanged a meaningful and mischievous look with Rowena.

Dean belted out a laugh and looked at Eileen. “Sammy not enough girl for you, huh?”

Cas reached around behind Jack and flicked Dean on the ear. “Be nice.”

Eileen rolled her eyes affectionately and said as she sighed dramatically, “Someone has to help me braid Sam’s hair.”

Sam groaned as he silently wished for a sinkhole to open up right beneath him and swallow him whole. He looked between the two women sat on either side of him. Rowena looked like she was going to eat him alive and Eileen simply smirked at him. _ Oh, god, I’m fucked. _

Jack seemed oblivious to the chaos he caused among the others at the table and continued when Sam didn’t answer him. “And my grandfather is--” Dean pinched Jack’s arm. ‘Ow! Oh, um… a… writer…”

Dean laughed nervously. “Don’t mind the kid. He had some minor surgery today so he’s kinda--” He crossed his eyes and made a circling motion to indicate loopiness.

Shelly laughed nervously. “Oh, um, ok just-- just holler if y’all need anything!” With that, she powerwalked to the hostess station.

Jack smiled. “She’s nice.” He commented. “We should make sure to give her a big tip. She deserves it.”

Eileen signed something lewd out of Jack’s line of sight that made Sam blush and Rowena grin wickedly at her two companions. “Oh she most certainly does, dearie.”

The rest of their meal was eaten in near silence, Shelly coming by only once to drop off the check, face aflame.

One awkward silent car ride home, Dean electing to rest while Sam drove, and they were home. As they all poured out of the car, Dean grabbed Jack and Cas by their respective jackets. “I need to make a serious supply run.” He grinned, eyes saying _ Take advantage of this free time, you sly dog you. _ “And you know what? We need a _ lot _ of supplies so I’ll take Jack and Cas with me. Might be gone several _ several _ hours.” He winked and turned back towards the Impala, Cas smiling encouragingly at Sam as he turned to get into the passenger seat and Jack just looking between Dean and Sam and tilting his head. Dean rolled the window down. “I’ll text you when we’re on our way home.” And with that, he sped off, leaving Sam red faced and alone between the two best women in his life.

Sam didn’t have much time to think too hard about what was about to happen. One second, he’s outside the bunker, the next he was inside, having been led there by Eileen and Rowena. They sat him down at the map table and smirked. “I think we broke him, the poor thing.” Rowena winked at Eileen, causing her to giggle. Eileen leaned down and started kissing Sam while Rowena nibbled at his ear.

Okay so maybe Jack was allowed to talk to strangers after all. Hell, if this was going to be the result, he could talk to every stranger they meet.

* * *

Later when all three had their energy spent and were satiated and snuggled together in Rowena’s bed, Sam looked down at the women in his arms. Both of them were sound asleep on either side of him. The sight made his heart clench.

Yes, he could get used to this.


End file.
